164648-60-6

Basic information

• Product Name: 1H-Benzimidazole-5-methanamine(9CI)
• Synonyms: 1H-Benzimidazole-5-methanamine(9CI);(1H-Benzo[d]iMidazol-5-yl)MethanaMine hydrochloride;benziMidazol-5-ylMethylaMine;(1H-benzo[d]iMidazol-5-yl)MethanaMine;C-(3H-Benzoimidazol-5-yl)-methylamine;(1H-benzimidazol-5-ylmethyl)amine dihydrochloride;(1H-benzo[d]imidazol-6-yl)methanamine
• CAS NO: 164648-60-6
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.1772
• Product Categories: BENZIMIDAZOLE
• Mol File: 164648-60-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 432.844 °C at 760 mmHg
• Flash Point: 245.506 °C
• Appearance: /
• Density: 1.279 g/cm³
• PKA: 12.79±0.10(Predicted)
• CAS DataBase Reference: 1H-Benzimidazole-5-methanamine(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-5-methanamine(9CI)(164648-60-6)
• EPA Substance Registry System: 1H-Benzimidazole-5-methanamine(9CI)(164648-60-6)

Safety Data

• Hazardous Substances Data: 164648-60-6(Hazardous Substances Data)

Usage

General Description

1H-Benzimidazole-5-methanamine(9CI) is a chemical compound with the molecular formula C8H9N3. It is a derivative of benzimidazole and is commonly used in the pharmaceutical industry for its potential antiviral and antimicrobial properties. The compound is a white solid in its pure form and is soluble in various organic solvents. It is also known to have potential use as a reagent in chemical synthesis and as a building block for the synthesis of various biologically active molecules. Studies have shown that 1H-Benzimidazole-5-methanamine(9CI) has the potential to inhibit certain enzymes and biological processes, making it a promising candidate for further research and development in the field of medicinal chemistry.

Synthetic route

(1H-benzo[d]imidazol-6-yl)methanol (106429-29-2) → 1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6)

Conditions	Yield
Stage #1: (1H-benzo[d]imidazol-6-yl)methanol With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 4h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 96h;	67%

5-(azidomethyl)benzimidazole (267875-43-4) → 1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6)

Conditions	Yield
With water; triphenylphosphine In tetrahydrofuran at 20℃;

5-benzimidazolecarboxylic acid (15788-16-6) → 1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 96 h / 0 - 20 °C 2.1: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 4 h / 20 °C 2.2: 96 h / 20 °C View Scheme

1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6) + 1,1'-carbonyldiimidazole (530-62-1) + 4-(4-Fluorophenoxy)piperidine hydrochloride → N-(1H-1,3-benzodiazol-6-ylmethyl)-4-(4-fluorophenoxy)piperidine-1-carboxamide (1392002-34-4)

Conditions	Yield
Stage #1: 1H-1,3-benzodiazol-6-ylmethanamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h; Stage #2: 4-(4-Fluorophenoxy)piperidine hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;	49%

1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6) + 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid → N-(1H-Benzimidazol-6-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide

Conditions	Yield
With 4-methyl-morpholine; ammonia; benzotriazol-1-ol In methanol; dichloromethane; N,N-dimethyl-formamide	10%

1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6) + 2-[3-({[(2 R)-1-Cyclopentylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2 H)-pyrazinyl]acetic acid hydrochloride (259538-84-6) → N-(1H-Benzimidazol-6-ylmethyl)-2-[3-({[(2R)-1-cyclopentylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide

1H-1,3-benzodiazol-6-ylmethanamine (164648-60-6) + 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid (1216142-18-5) → N-((1H-benzo[d]imidazol-6-yl)methyl)-6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;

Upstream product

• 267875-43-4 6-azidomethyl-1H-benzo [d]imidazole 
• 106429-29-2 (1H-benzo[d]imidazol-6-yl)methanol 
• 15788-16-6 5-benzimidazolecarboxylic acid 

Downstream Products

• 1392002-34-4 N-(1H-1,3-benzodiazol-6-ylmethyl)-4-(4-fluorophenoxy)piperidine-1-carboxamide 

Relevant articles and documents

PROTEASE ACTIVATED RECEPTOR 2 (PAR2) ANTAGONISTS

A compound of formula (I) or a pharmaceutically acceptable salt, solvate, hydrate thereof (I) Wherein Y, Z, R3, U, R4, m and n are as defined in the claims.